7284-16-4 Usage
Description
P-NITROPHENYL BETA-D-N,N'-DIACETYLCHITOBIOSE, also known as 4-Nitrophenyl N,N-Diacetyl-β-D-chitobioside (CAS# 7284-16-4), is an off-white solid compound that is useful in organic synthesis. It is a derivative of chitobiose, a disaccharide composed of two N-acetyl-D-glucosamine units, and is commonly utilized in the study and measurement of various enzymatic activities.
Uses
1. Used in Enzyme Activity Measurement:
P-NITROPHENYL BETA-D-N,N'-DIACETYLCHITOBIOSE is used as a substrate for measuring the exochitinase activity of various proteins and enzymes. This application is particularly relevant in the study of chitinolytic enzymes, such as N-acetyl-β-D-glucosaminidases, which play a crucial role in the degradation of chitin, a major component of the exoskeleton of arthropods and the cell walls of fungi.
2. Used in Organic Synthesis:
As a compound useful in organic synthesis, P-NITROPHENYL BETA-D-N,N'-DIACETYLCHITOBIOSE can be employed in the development of new chemical compounds and materials. Its unique structure and reactivity make it a valuable building block for the synthesis of various organic molecules, potentially leading to novel applications in different industries.
3. Used in Pharmaceutical Research:
P-NITROPHENYL BETA-D-N,N'-DIACETYLCHITOBIOSE may also be used in the pharmaceutical industry for the development of new drugs targeting chitinolytic enzymes. By understanding the interactions between this compound and specific enzymes, researchers can potentially design more effective drugs for the treatment of various diseases and conditions related to chitin metabolism.
4. Used in Agricultural Applications:
In the agricultural industry, P-NITROPHENYL BETA-D-N,N'-DIACETYLCHITOBIOSE could be employed as a tool for studying the chitinolytic enzymes involved in the breakdown of chitin in pests and pathogens. This knowledge can be applied to develop more targeted and environmentally friendly pest control strategies, reducing the reliance on chemical pesticides.
5. Used in Environmental Research:
P-NITROPHENYL BETA-D-N,N'-DIACETYLCHITOBIOSE can also be utilized in environmental research to study the role of chitinolytic enzymes in the breakdown of chitin in natural ecosystems. This information can contribute to a better understanding of nutrient cycling and the role of chitin in maintaining ecological balance.
Biochem/physiol Actions
4-Nitrophenyl N,N′-diacetyl-β-D-chitobioside is a substrate for determining exochitinase activity (chitobiosidase activity).
Check Digit Verification of cas no
The CAS Registry Mumber 7284-16-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,2,8 and 4 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 7284-16:
(6*7)+(5*2)+(4*8)+(3*4)+(2*1)+(1*6)=104
104 % 10 = 4
So 7284-16-4 is a valid CAS Registry Number.
7284-16-4Relevant articles and documents
How Site-Directed Mutagenesis Boosted Selectivity of a Promiscuous Enzyme
Nekvasilová, Pavlína,Kulik, Natalia,Rychlá, Nikola,Pelantová, Helena,Petrásková, Lucie,Bosáková, Zuzana,Cva?ka, Josef,Slámová, Kristyna,K?en, Vladimír,Bojarová, Pavla
, p. 4138 - 4150 (2020)
β-N-Acetylhexosaminidases (GH20; EC 3.2.1.52) are exo-glycosidases with a dual activity for cleaving both N-acetylglucosamine (GlcNAc) and N-acetylgalactosamine (GalNAc) units from glycostructures. This substrate promiscuity is a hurdle in the selective synthesis of N-acetylhexosamine oligosaccharides combining both GlcNAc and GalNAc units since there are hardly any GalNAc transferring enzymes available for synthetic applications. We present here site-directed mutagenesis of a synthetically potent promiscuous β-N-acetylhexosaminidase from Talaromyces flavus (TfHex), which, as a wild type, exhibits a GalNAcase/GlcNAcase ratio of 1.2. On the basis of molecular modeling, we identified crucial amino acid residues responsible for its GalNAcase/GlcNAcase selectivity. Six site-directed mutants were prepared, heterologously expressed in Pichia pastoris, purified, and kinetically characterized. As a result, novel engineered enzymes with an up to 7-times higher selectivity for either GalNAc or GlcNAc substrates were obtained, preserving the favorable properties of the wild type TfHex, mainly its transglycosylation potential and tolerance to functional groups in the substrate molecule. The substrate selectivity and transglycosylation yield were further corroborated by reaction engineering. The new selective and synthetically capable enzymes were applied in the preparation of tailored N-acetylhexosamines. (Figure presented.).
Direct Synthesis of para-Nitrophenyl Glycosides from Reducing Sugars in Water
Fairbanks, Antony J.,Qiu, Xin
supporting information, (2020/03/24)
Reducing sugars may be directly converted into the corresponding para-nitrophenyl (pNP) glycosides using 2-chloro-1,3-dimethylimidazolinium chloride (DMC), para-nitrophenol, and a suitable base in aqueous solution. The reaction is stereoselective for sugars with either a hydroxyl or an acetamido group at position 2, yielding the 1,2-trans pNP glycosides. A judicious choice of base allows extension to di-and oligosaccharide substrates, including a complex N-glycan oligosaccharide isolated from natural sources, without the requirement of any protecting group manipulations
Enzymatic synthesis of p-nitrophenyl β-chitobioside
Kubisch, Jiri,Weignerova, Lenka,Koetter, Sven,Lindhorst, Thisbe K.,Sedmera, Petr,Kren, Vladimir
, p. 975 - 984 (2007/10/03)
p-Nitrophenyl β-chitobioside (2) was prepared from p-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside (1) using β-N-acetylhexosaminidase from Aspergillus oryzae. As minor by-product a (1→6)-linked regioisomer (3a) was formed. Addition of (NH4/sub
